Sugar chain array

ABSTRACT

A sugar chain array containing a sugar chain immobilized thereon for detecting binding between an analyte and a sugar chain, and a sugar chain array having the sugar chain immobilized thereon that is capable of inhibiting non-specific adsorption and binding of an analyte without having to coat the array with an adsorption inhibitor. A specific sugar chain is immobilized on the array, and is useful for detecting binding between the sugar chain and an analyte, such as a pathogen of an infectious disease or an excretion thereof. In addition, in the array, when a base material is coated with a polymeric compound having a unit having a primary amino group, a unit for maintaining hydrophilicity, and a unit having a hydrophobic group, the sugar chain is immobilized efficiently and non-specific adsorption and binding of the analyte can be effectively inhibited.

TECHNICAL FIELD

The present invention relates to a sugar chain array capable ofdetecting binding between an analyte and a sugar chain.

BACKGROUND ART

In the field of biochemistry, sugar chains have attracted attention inrecent years as a third type of chain following nucleic acids andproteins. In particular, research has been conducted on theirinvolvement with cell differentiation and malignant transformation,immune response and fertilization, and attempts are continuing towardsthe development of new pharmaceuticals and medical materials.

In addition, sugar chains serve as receptors for numerous toxins,viruses and bacteria and are also attracting attention as tumor markers,and attempts are similarly continuing towards the development of newpharmaceuticals and medical materials in these fields as well.

However, although the importance of research on sugar chains isrecognized, due to their complex structure and diversity, the pace atwhich this research has progressed is considerably slower in comparisonwith the first and second types of chains in the form of nucleic acidsand proteins.

The objective of proceeding with this research is to develop variousmethods for purifying sugar chains. In addition, since numerous cases ofsugar chains functioning as ligands for cell receptors have beenconfirmed rather than these sugar chains functioning independently,development has also proceeded on base materials for immobilizingvarious sugar chains to enable them to be used in analyzing sugar chainreceptors (Patent Document 1, Patent Document 2).

Patent Document 1 indicates a method for producing a sugar chain arrayin which a sugar chain is bound to a first functional group, and a thirdfunctional group is bound to a chromophore by using a second functionalgroup as a solid support. It is described in the examples thereof that ablocking procedure is carried out using bovine serum albumin in order toprevent non-specific adsorption following sugar chain immobilization.However, carrying out this blocking procedure following sugar chainimmobilization is both complicated and troublesome.

On the other hand, Patent Document 2 describes a method for immobilizinga sugar chain on a base material through a spacer, and indicates thatnon-specific adsorption is inhibited by using a hydrophilic compound forthe spacer. However, in this method, it is necessary to introduce anacetyl halide group into the solid support when immobilizing the sugarchain on the base material, and although this is comparatively easy inthe case the material of the base material is glass, this method lacksversatility with respect to other materials.

In this manner, in addition to delays in the development of suitabletechniques and base materials for immobilizing sugar chains, developmenthas also been delayed with respect to sugar chain arrays on which sugarchains are immobilized that are useful for analyzing interactionsbetween analytes and sugar chains.

PRIOR ART DOCUMENTS Patent Documents

-   [Patent Document 1] Japanese Unexamined Patent Application, First    Publication No. 2004-115616-   [Patent Document 2] Japanese Unexamined Patent Application, First    Publication No. 2006-078418

DISCLOSURE OF THE INVENTION Problems to be Solved by the Invention

With the foregoing in view, an object of the present invention is toprovide a sugar chain array having a sugar chain immobilized thereonthat is useful for detecting binding between an analyte and a sugarchain. Another object of the present invention is to provide a sugarchain array having the aforementioned sugar chain immobilized thereonthat is capable of inhibiting non-specific adsorption and binding of ananalyte without having to coat the sugar chain array with an adsorptioninhibitor.

Means for Solving the Problems

As a result of conducting extensive studies to achieve theaforementioned objects, the inventors of the present invention foundthat a sugar chain array having the sugar chains described in thefollowing Tables 1 to 6 immobilized thereon is useful for detectinginteraction between the sugar chains and analytes such as pathogens ofinfectious diseases and secretions thereof. Moreover, the inventors ofthe present invention found that, when a base material coated with apolymeric compound comprising a unit having a primary amine group, aunit for maintaining hydrophilicity, and a unit having a hydrophobicgroup is used in this sugar chain array, the sugar chain is immobilizedefficiently and non-specific adsorption and binding of the analyte canbe effectively inhibited, thereby leading to completion of the presentinvention.

More specifically, the present invention provides the inventionsindicated below.

[1] A sugar chain array comprising a base material and at least onesugar chain selected from the group consisting of sugar chains describedin the following Tables 1 to 6:

TABLE 1 1 Glc Acyl1-O-6Glc 2 Galβ1-4Glc Xyl 3 Gal Galα1-4Gal 4GalNAcα1-3GalNAcβ1-3Galα1-4Gal Galα1-4Galβ1-4Glc 5Galα1-3Galα1-4Galβ1-4Glc Galα1-3Galα1-3Galα1-4Galβ1-4Glc 6Galα1-3Galα1-3Galα1-3Galα1-4Galβ1-4Glc GalNAcβ1-3Galα1-4Galβ1-4Glc 7GalNAcα1-3GalNAcβ1-3Galα1-3Galβ1-4Glc Galβ1-3GalNAcβ1-3Galα1-4Galβ1-4Glc8 GalNAcβ1-3Galα1-3Galα1-4Glc GalNAcβ1-3Galα1-3Galα1-3Galα1-4Glc 9GalNAcβ1-3Galα1-3Galα1-3Galα1-3Galα1- Galα1-3Galβ1-4Glc 4Galβ1-4Glc 10GalNAcβ1-3Galα1-3Galβ1-4Glc GlcNAcβ1-3Galβ1-4Glc 11Galβ1-3GlcNAcβ1-3Galβ1-4Glc Galβ1-4GlcNAcβ1-3Galβ1-4Glc 12Galα1-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc Galβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc 13Galα1-4Galβ1-4GlcNAcβ1-3Galβ1-4GlcGalβ1-4GlcNAcβ1-3Galβ1-4GlcNAcβ1-3Galβ1- 4Glc 14GalNAcβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc Galα1-3Galβ1-4GlcNAcβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc 15 Galβ1-4GlcNAcβ1-3(Galβ1-4GlcNAcβ1-GalNAcα1-3Galβ1-4GlcNAcβ1-3(Galβ1- 6)Galα1-4GlcNAcβ1-3Galβ1-4Glc4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4Glc 16Galα1-3Galβ1-4GlcNAcβ1-3(Galα1-3Galβ1-Galα1-3Galβ1-4GlcNAcβ1-3(Galα1-3Galβ1-4GlcNAcβ1-6)Galα1-4GlcNAcβ1-3Galβ1-4Glc4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3(Galα1- 3Galβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4Glc 17 GalNAcβ1-4Galβ1-4Glc Galβ1-3GalNAcβ1-4Galβ1-4Glc 18GlcNAcβ1-3(GalNAcβ1-4)Galβ1-4Glc Galα1-3Galβ1-4GlcNAcβ1-3(GalNAcβ1-4)Galβ1-4Glc 19 HSO3-3Glc HSO3-3Galβ1-4Glc 20 HSO3-3GalHSO3-3GalNAcβ1-3Galα1-4Galβ1-4Glc 21HSO3-3Galβ1-3GaNAcβ1-3Galα1-4Galβ1-4Glc GalNAcβ1-4(HSO3-3)Galβ1-4Glc 22HSO3-3GalNAcβ1-4(HSO3-3)Galβ1-4Gal Galβ1-3GalNAcβ1-4(HSO3-3)Galβ1-4Glc23 HSO3-3Galβ1-3GalNAcβ1-4Galβ1-4GlcHSO3-3Galβ1-3GalNAcβ1-4(HSO3-3)Galβ1- 4Glc 24 HSO3-6GlcNAcβ1-3Galβ1-4GlcGalβ1-4(HSO3-6)GlcNAcβ1-3Galβ1-4Glc 25HSO3-3GlcUAβ1-3Galβ1-4GlcNAcβ1-3Galβ1-HSO3-3GlcUAβ1-3(Galβ1-4GlcNAcβ1)₂- 4Glc 3Galβ1-4Glc 26HSO3-3Gal1-4Gal1-4Glc Fuc

TABLE 2 27 Fucα1-2Galβ1-4Glc GalNAcα1-3(Fucα1-2)Galβ1-4Glc 28Fucα1-2Galα1-3Galα1-4Galβ1-4Glc Fucα1-2Galβ1-3GalNAcβ1-3Galα1-4Galβ1-4Glc 29 Galβ1-4(Fucα1-3)GlcNAcβ1-6(Galβ1- Fucα1-2Galα1-3Galβ1-4Glc3)GalNAcβ1-3Galα1-4Galβ1-4Glc 30 Galα1-3(Fucα1-2)Galβ1-4GlcGalα1-3(Fucα1-2)Galβ1-3GalNAcβ1-3Galα1- 3Galβ1-4Glc 31Fucα1-2Galβ1-3GalNAcβ1-4Galβ1-4Glc Galα1-3Galβ1-3GalNAcβ1-4Galβ1-4Glic32 Galα1-3(Fucα1-2)Galβ1-3GalNAcβ1-3Galβ1-Fucα1-2Galβ1-3Glcp1-3Galβ1-4Glc 4Glc 33Galβ1-3(Fucα1-4)GlcNAcβ1-3Galβ1-4GlcGalα1-3(Fucα1-2)Galβ1-3GlcNAcβ1-3Galβ1- 4Glc 34GalNAcα1-3(Fucα1-2)Galβ1-3GlcNAcβ1-Fucα1-2Galβ1-3(Fucα1-4)GlcNAcβ1-3Galβ1- 3Galβ1-4Glc 4Glc 35Galα1-3(Fucα1-2)Galβ1-3(Fucα1- GalNAcα1-3(Fucα1-2)Galβ1-3(Fucα1-4)GlcNAcβ1-3Galβ1-4Glc 4)GlcNAcβ1-3Galβ1-4Glc 36Fucβ1-2Galβ1-4GlcNAcβ1-3Galβ1- Galβ1-3(Fucα1-4)GlcNAcβ1-3Galβ1-3GlcNAcβ1-3Galβ1-4Glc 3GlcNAcβ1-3Galβ1-4Glc 37Fucα1-2Galβ1-4(Fucβ1-3)GlcNAcβ1-3Galβ1-Fucα1-2Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1- 3GlcNAcβ1-3Galβ1-4Glc3(Fucα1-4)GlcNAcβ1-3Galβ1-4Glc 38 Fucα1-2Galβ1-3GlcNAcβ1-3(Fucα1-2Galβ1-GalNAcα1-3(Fucα1-2)Galβ1-3GlcNAcβ1-3(4)GlcNAcβ1-6)Galβ1-3GlcNAcβ1-3Galβ1-3(GalNAcα1-3(Fucα1-4)Galβ1-3GlcNAcβ1- 4Glc 6)Galβ1-3GlcNAcβ1-3Galβ1-4Glc39 GalNAcα1-3(Fucα1-2)Galβ1-3GlcNAcβ1-Fucα1-2Galβ1-4GlcNAcβ1-3Galβ1-4Glc 3(GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-6)Galβ1-3GlcNAcβ1-3Galβ1-4Glc 40 Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-4GlcGalα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-3Galβ1- 4Glc 41GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-Fucα1-2Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1- 3Galβ1-4Glc 4Glc 42Fucα1-2Galβ1-4GlcNAcβ1-3Galβ1- GalNAcα1-3(Fucα1-2)Galβ1-4(Fucα1-4GlcNAcβ1-3Galβ1-4Glc 3)GlcNAcβ1-3Galβ1-4Glc 43Galα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-3Galβ1-GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1- 4GlcNAcβ1-3Galβ1-4Glc3Galβ1-4GlcNAcβ1-3Galβ1-4Glc 44 Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-4(Fucα1-Fucα1-2Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1- 3)GlcNAcβ1-3Galβ1-4Glc4GlcNAcβ1-3Galβ1-4Glc 45 Fucα1-2Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-Fucα1-2Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1- 4GlcNAcβ1-3Galβ1-4Glc4(Fucα1-3)GlcNAcβ1-3Galβ1-4Glc 46 Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-Galβ1-4GlcNAcβ1-3Galβ1-4(Fucα1- 4GlcNAcβ1-3Galβ1-4Glc3)GlcNAcβ1-3Galβ1-4Glc 47 Galβ1-3GalNAcα1-3(Fucα1-2)Galβ1 -Galβ1-3(Fucα1-4)GlcNAcβ1-3Galβ1- 4GlcNAcβ1-3Galβ1-4Glc4GlcNAcβ1-3Galβ1-4Glc

TABLE 3 48 GalNAcα1-3(Fucα1-2)Galβ1-3GalNAcα1-Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1- 3(Fucα1-2)Galβ1-4GlcNAcβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc 4GlcNAcβ1-3Galβ1-4Glc 49Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-4(Fucα1-Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc3)GlcNAcβ1-3Galβ1-4(Fucα1-3)GlcNAcβ1- 3Galβ1-4Glc 50Galβ1-4GlcNAcβ1-3Galβ1-4(Fucα1- Fucα1-2Galβ1-4GlcNAcβ1-3(Fucα1-2Galβ1-3)GlcNAcβ1-(3Galβ1-4GlcNAcβ1)2-3Galβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4Glc 4Glc 51GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-Galα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-3(Galα1-3(GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1- 3(Fucα1-2)Galβ1-4GlcNAcβ1-6)Galβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4Glc 4GlcNAcβ1-3Galβ1-4Glc 52GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-Galα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-3Galβ1-3Galβ1-4GlcNAcβ1-3(GalNAcα1-3(Fucα1- 4GlcNAcβ1-3(Galα1-3(Fucα1-2)Galβ1-2)Galβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4Glc 3Galβ1-4Glc 53Galα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-3(Galα1- Fucα1-3GalNAcβ1-3Galα1-3Galβ1-3(Fucα1-2)Galβ1-4GlcNAcβ1-6)Galβ1- 4GlcNAcβ1-3(GlcNAcβ1-4)Galβ1-4Glc4GlcNAcβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc 54GalNAcα1-3(Fucα1-2)Galβ1-3Galβ1-4Galβ1-GalNAcα1-3(Fucα1-2)Galβ1-3(4)GlcNAcβ1- 4Glc 3Galβ1-4Glc 55GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-GalNAcα1-3(Fucα1-2)Galβ1-4Galβ1-3(Galβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4Galβ1-4Glc 6)Galβ1-4Glc 56GalNAcα1-3(Fucα1-2)Galβ1-4Galβ1- GalNAcα1-3(Fucα1-2)Galβ1-3(GalNAcα1-3(GalNAcα1-3Galβ1-6)Galβ1-4Glc 3Galβ1-6)Galβ1-4Galβ1-4Glc 57GalNAcα1-3(Fucα1-2)Galβ1-4Galβ1- Galβ1-4(Fucα1-3)GlcNAcβ1-4Galβ1-3Galβ1-3(GlcNAcα1-4Galβ1-6)Galβ1-4Glc 4Glc 58GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1- GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-3(GlcNAcβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3(GlcNAcβ1-4GlcNAcβ1-4)(GalNAcα1- 4GlcNAcβ1-3(GlcNAcβ1-6)Galβ1-4Glc3(Fucα1-2)Galβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-4GlcNAcβ1-3(GlcNAcβ1-4Galβ1- 4GlcNAcβ1-3)Galβ1-4Glc 59GalNAcα1-3(Fucα1-2)Galβ1-3(4)GlcNAcβ1- NeuAcα2-3Gal3(Fucα1-2Galβ1-3(4)GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3(Galβ1-4GlcNAcβ1-3(Galβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-6)Galβ1- 4Galβ1-4Glc 60 NeuGcα2-3GalNeuAcα2-3Galβ1-4Glc 61 NeuGcα2-3Galβ1-4Glc NeuNH2α2-3Galβ1-4Glc 62Ac—O-4NeuGcα2-3Galβ1-4Glc NeuAcα2-8NeuAcα2-3Galβ1-4Glc 63NeuGcα2-8NeuAcα2-3Galβ1-4Glc NeuAcα2-8NeuGcα2-3Galβ1-4Glc 64NeuGcα2-8NeuGcα2-3Galβ1-4Glc Ac—O-9NeuAcα2-8NeuAcα2-3Galβ1-4Glc

TABLE 4 65 NeuAcα2-8NeuAcα2-8Neuα2-3Galβ1-4GlcAc—O-9NeuAcα2-8NeuAcα2-8NeuAcα2- 3Galβ1-4Glc 66GalNAcβ1-4(NeuAcα2-3)Galβ1-4Glc GalNAcβ1-4(NeuGcα2-3)Galβ1-4Glc 67Galβ1-3GalNAcβ1-4(NeuAcα2-3)Galβ1-4GlcGalβ1-3GalNAcβ1-4(NeuGcα2-3)Galβ1-4Glc 68Fucα1-2Galβ1-3GalNAcβ1-4(NeuAcα2- Fucα1-2Galβ1-3GalNAcβ1-4(NeuGcα2-3)Galβ1-4Glc 3)Galβ1-4Glc 69 Fucα1-3Galβ1-3GalNAcβ1-4(NeuAcα2-Galα1-3Galβ1-3GalNAcβ1-4(NeuAcα2- 3)Galβ1-4Glc 3)Galβ1-4Glc 70GalNAcβ1-4Galβ1-3GalNAcβ1-4(NeuAcα2-GalNAcα1-3GalNAcβ1-3Galβ1-3GalNAcβ1- 3)Galβ1-4Glc 4(NeuAcα2-3)Galβ1-4Glc71 Galβ1-3(Fucα1-2)Galβ1-3GalNAcβ1- Galβ1-3Galα1-3Galβ1-3GalNAcβ1-4(NeuAcα2-3)Galβ1-4Glc 4(NeuAcα2-3)Galβ1-4Glc 72Galα1-3Galβ1-3Galα1-3Galβ1-3GalNAcβ1-NeuAcα2-3Galβ1-3GalNAcβ1-4(NeuAcα2- 4(NeuAcα2-3)Galβ1-4Glc 3)Galβ1-4Glc73 NeuAc(NeuGc)α2-3Galβ1-3GalNAcβ1- NeuGcα2-3Galβ1-3GalNAcβ1-4NeuGcα2-4(NeuGc(NeuAc)α2-3)Galβ1-4Glc 3Galβ1-4Glc 74NeuAc9—O—Acα2-3Galβ1-3GalNAcβ1- GalNAcβ1-4(NeuAcα2-3)Galβ1-3GalNAcβ1-4(NeuAcα2-3)Galβ1-4Glc 4(NeuAcα2-3)Galβ1-4Glc 75NeuAcα2-8NeuAcα2-3Galβ1-3GalNAcβ1- GalNAcβ1-4(NeuAcα2-8NeuAcα2-3)Galβ1-4(NeuAcα2-3)Galβ1-4Glc 4Glc 76 Galβ1-3GalNAcβ1-4(NeuAcα2-8NeuAcα2-Fucα1-2Galβ1-3GalNAcβ1-4(NeuAcα2- 3)Galβ1-4Glc 8NeuAcα2-3)Galβ1-4Glc 77Galα1-3Galβ1-3GalNAcβ1-4(NeuAcα2- Galα1-3Galα1-3Galβ1-3GalNAcβ1-8NeuAcα2-3)Galβ1-4Glc 4(NeuAcα2-8NeuAcα2-3)Galβ1-4Glc 78Galα1-3(Fucα1-2)Galβ1-3GalNAcβ1- NeuAcα2-3Galβ1-3GalNAcβ1-4(NeuAcα2-4(NeuAcα2-8NeuAcα2-3)Galβ1-4Glc 8NeuAcα2-3)Galβ1-4Glc 79NeuAcα2-3Galβ1-3GalNAcβ1-4(NeuAc9—O— NeuAcα2-8NeuAcα2-3Galβ1-3GalNAcβ1-Acα2-8NeuAcα2-3)Galβ1-4Glc 4(NeuAcα2-8NeuAcα2-3)Galβ1-4Glc 80GalNAcβ1-4(NeuAcα2-8NeuAcα2-8NeuAcα2-Galβ1-3GalNAcβ1-4(NeuAcα2-8NeuAcα2- 3)Galβ1-4Glc 8NeuAcα2-3)Galβ1-4Glc81 NeuAcα2-3Galβ1-3GalNAcβ1-4(NeuAcα2-NeuAcα2-8NeuAcα2-3Galβ1-3GalNAcβ1- 8NeuAcα2-8NeuAcα2-3)Galβ1-4Glc4(NeuAcα2-8NeuAcα2-8NeuAcα2-3)Galβ1- 4Glc 82NeuAcα2-3Galβ1-3GalNAcβ1-4Galβ1-4GlcNeuGcα2-3Galβ1-3GalNAcβ1-4Galβ1-4Glc 83GalNAcβ1-4(NeuAcα2-3)Galβ1-3GalNAcβ1-GalNAcβ1-4(NeuGcα2-3)Galβ1-3GalNAcβ1- 4Galβ1-4Glc 4Galβ1-4Glc 84Galβ1-3GalNAcβ1-4(NeuGcα2-3)Galβ1-Galβ1-3(NeuAcα2-6)GalNAcβ1-4Galβ1-4Glc 3GalNAcβ1-4Galβ1-4Glc

TABLE 5 85 NeuAcα2-3Galβ1-3(NeuAcα2-6)GalNAcβ1-NeuAcα2-3Galβ1-3(NeuAcα2-8NeuAcα2- 4Galβ1-4Glc 6)GalNAcβ1-4Galβ1-4Glc 86NeuAcα2-8NeuAcα2-3Galβ1-3(NeuAcα2- NeuAcα2-8NeuAcα2-3Galβ1-3(NeuAcα2-6)GalNAcβ1-4Galβ1-4Glc 8NeuAcα2-6)GalNAcβ1-4Galβ1-4Glc 87NeuAcα2-3Galβ1-3(NeuAcα2-6)GalNAcβ1-NeuAcα2-3Galβ1-3GalNAcβ1-3Galα1-4Galβ1- 4(NeuAcα2-3)Galβ1-4Glc 4Glc 88NeuGcα2-3Galβ1-3GalNAcβ1-3Galα1-4Galβ1-NeuAcα2-8NeuAcα2-3Galβ1-3GalNAcβ1- 4Glc 3Galα1-4Galβ1-4Glc 89NeuGcα2-8NeuGcα2-3Galβ1-3GalNAcβ1- NeuAcα2-3Galβ1-3(NeuAcα2-6)GalNAcβ1-3Galα1-4Galβ1-4Glc 3Galα1-4Galβ1-4Glc 90NeuAcα2-3Galβ1-3GalNAcβ1-3Galα1-3Galβ1-NeuAcα2-3Galβ1-3GlcNAcβ1-3Galβ1-4Glc 4Glc 91NeuAcα2-3Galβ1-3(Fucα1-4)GlcNAcβ1- GalNAcβ1-4(NeuAcα2-3)Galβ1-3GlcNAcβ1-3Galβ1-4Glc 3Galβ1-4Glc 92 NeuAcα2-3Galβ1-3Galβ1-3GlcNAcβ1-3Galβ1-NeuAcα2-3Galβ1-3(NeuAcα2-6)GlcNAcβ1- 4Glc 3Galβ1-4Glc 93NeuAcα2-3Galβ1-3(Fucα1-4))(NeuAcα2- NeuAcα2-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc6)GlcNAcβ1-3Galβ1-4Glc 94 NeuGcα2-3Galβ1-4GlcNAcβ1-3Galβ1-4GlcNeuAcα2-6Galβ1-4GlcNAcβ1-3Galβ1-4Glc 95NeuAcα2-8NeuAcα2-3Galβ1-4GlcNAcβ1- NeuGcα2-8NeuGcα2-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc 3Galβ1-4Glc 96 NeuAcα2-8NeuGcα2-3Galβ1-4GlcNAcβ1-NeuAcα2-8NeuAcα2-8NeuAcα2-3Galβ1- 3Galβ1-4Glc 4GlcNAcβ1-3Galβ1-4Glc 97GalNAcβ1-4(NeuAcα2-3)Galβ1-4GlcNAcβ1- NeuAcα2-3Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-4Glc 3Galβ1-4Glc 98 NeuAcα2-6Galβ1-4GlcNAcβ1-3(Galβ1-NeuAcα-3Galβ1-4GlcNAcβ1-3Galβ1- 4GlcNAcβ1-6)Galβ1-4Glc4GlcNAcβ1-3Galβ1-4Glc 99 NeuGcα2-3Galβ1-4GlcNAcβ1-3Galβ1-NeuAcα2-6Galβ1-4GlcNAcβ1-3Galβ1- 4GlcNAcβ1-3Galβ1-4Glc4GlcNAcβ1-3Galβ1-4Glc 100 NeuAcα2-3Galβ1-4GlcNAcβ1-(3Galβ1-NeuAcα2-3Galβ1-4GlcNAcβ1-3Galβ1- 4GlcNAcβ1)2-3Galβ1-4Glc4(Fucα1-3)GlcNAcβ1-3Galβ1-4Glc 101 NeuAcα2-3Galβ1-4GlcNAcβ1-3Galβ1-NeuAcα2-3Galβ1-4GlcNAcβ1-3Galβ1- 4(Fucα1-3)GlcNAcβ1-3Galβ1-4GlcNAcβ1-4(Fucα1-3)GlcNAcβ1-(3Galβ1-4GlcNAcβ1)2- 3Galβ1-4Glc 3Galβ1-4Glc 102NeuAcα2-3Galβ1-3GalNAcα1-3(Fucα1- NeuAcα2-3Galβ1-4GlNAcα1-3(Galβ1-2)Galβ1-4GlcNAcβ1-3Galβ1-4Glc 4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4Glc103 NeuAcα2-3Galβ1-4GlcNAcα1-3(Fucα1-NeuAcα2-3Galβ1-4GlcNAcα1-3(NeuAcα2- 2Galβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1- 3Galβ1-4Glc 3Galβ1-4Glc

TABLE 6 104 NeuAcα2-3Galβ1-4GlcNAcβ1-3Galβ1-NeuAcα2-3Galβ1-4GlcNAcβ1-3(NeuAcα2-3Galβ1-4GlcNAcβ1-3(6)(NeuAcα2-3Galβ1-4GlcNAcβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3(6)(NeuAcα2-3(6))Galβ1-4GlcNAcβ1-3Galβ1-4Glc3Galβ1-4GlcNAcβ1-3(6))Galβ1-4GlNAcβ1-3Galβ1- 4Glc 105NeuAcα2-3Galβ1-4GlcNAcβ1-3(Galα1-3Galβ1-NeuAcα2-3Galβ1-4GlcNAcβ1-3(GalNAcβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4Glc 4)Galβ1-4Glc 106GalNAcβ1-4(NeuAcα2-3)Galβ1-4GlcNAcβ1- NeuAcα2-3Galβ1-3GalNAcβ1-4Glc3(GalNAcβ1-4)Galβ1-4Glc 107 GalNAcα1-3(Fucα1-2)Galβ1-3GalNAcβ1-Galα1-3(Fucα1-2)Galβ1-3GalNAcβ1-3Galα1- 3Galα1-4Galβ1-4Glc 4Galβ1-4Glc108 Neu5Acα2-3Galβ1-3GalNAcβ1-3Gal GalNAcα1-3GalNAcβ1-3Galα1-4Galβ1-4Glc

wherein, the sugar chain is immobilized on the base material.

[2] The sugar chain array described in [1], wherein the base material iscoated with a polymeric compound containing a unit having a primaryamino group, and a sugar chain is immobilized on the base material bybonding the primary amino group to a reducing group on the end of thesugar chain.

[3] The sugar chain array described in [2], wherein the polymericcompound further contains a unit for maintaining hydrophilicity and aunit having a hydrophobic group.

[4] The sugar chain array described in [3], wherein the polymericcompound is represented by the following general formula [1]:

(wherein, R1, R2 and R3 represent hydrogen atoms or methyl groups, R4represents a hydrophobic group, X represents an alkyleneoxy group having1 to 10 carbon atoms, p represents an integer of 1 to 20 and in the casep is an integer of 2 to 20, the repeating X may be the same ordifferent, Y represents a spacer containing an alkylene glycol residue,Z represents an oxygen atom or NH, and l, m and n represent naturalnumbers).

[5] The sugar chain array described in [4], wherein, in the polymericcompound represented by general formula [1], Y is represented by thefollowing general formula [2] or general formula [3]:

(wherein, q and r represent integers of 1 to 20)

(wherein, q and r represent integers of 1 to 20).

[6] The sugar chain array described in any of [2] to [5], wherein theprimary amino group in the polymeric compound is an oxylamino groupand/or hydrazide group.

[7] The sugar chain array described in [6], wherein the content of theunit having a primary amino group in the polymeric compound is 20 mol %to 40 mol % of all units of the polymeric compound.

[8] The sugar chain array described in [4], wherein X represents anethyleneoxy group in general formula [1].

[9] The sugar chain array described in any of [2] to [8], wherein themain chain of the polymeric compound is a (meth)acrylic backbone.

[10] The sugar chain array described in [4], wherein the hydrophobicgroup R4 in general formula [1] is an alkyl group having 2 to 10 carbonatoms.

[11] The sugar chain array described in [10], wherein the hydrophobicgroup R4 in general formula [1] is a cyclic alkyl group.

[12] The sugar chain array described in [11], wherein the cyclic alkylgroup is a cyclohexyl group.

Effects of the Invention

Use of the sugar chain array of the present invention makes it possibleto efficiently detect interaction between an analyte and a sugar chain.In particular, in this sugar chain array, by using a base materialcoated with a polymeric compound containing a unit having a primaryamino group, a unit for maintaining hydrophilicity, and a unit having ahydrophobic group, the sugar chain can be immobilized efficiently andnon-specific adsorption and binding of the analyte can be inhibited.

BEST MODE FOR CARRYING OUT THE INVENTION

The present invention provides a sugar chain array having at least onesugar chain selected from the group composed of sugar chains describedin the aforementioned Tables 1 to 6 immobilized on a base material. Thesugar chain array of the present invention can be used to detect bindingbetween a sugar chain and an analyte (desired substance for detectingbinding with, for example, a protein such as lecthin, a pathogen of aspecific infectious disease and a secretion thereof, or other sugarchain). For example, since sugar chains among the sugar chains describedin the aforementioned Tables 1 to 6 that contain sialic acid on anon-reducing terminal are recognized by influenza virus, an array havingthese sugar chains immobilized thereon is useful for diagnosinginfection by influenza virus or developing a therapeutic drug againstinfluenza virus. In addition, since sugar chains among the sugar chainsdescribed in the aforementioned Tables 1 to 6 that haveN-acetyllactosamine and a repeating structure thereof bind withgalectin, which has been suggested to be related to diseases such ascancer, an array having these sugar chains immobilized thereon is usefulfor diagnosing diseases such as cancer or developing a therapeutic drugagainst diseases such as cancer. The sugar chain array of the presentinvention preferably has two or more of the sugar chains selected fromthe group consisting of the sugar chains described in the aforementionedTables 1 to 6 immobilized thereon (and for example, 5 or more, 10 ormore, 30 or more, 50 or more, 100 or more, 150 or more or 200 or more).

The base material in the sugar chain array of the present invention ispreferably coated with a polymeric compound containing a unit having aprimary amino group. A sugar chain can be immobilized on the basematerial by bonding the primary amino group in the base material to areducing terminal of the sugar chain.

The polymeric compound in the base material preferably further containsa unit for maintaining hydrophilicity and a unit having a hydrophobicgroup. In this form of base material, the unit for maintaininghydrophilicity fulfills the role of inhibiting physical adsorption(non-specific adsorption) of an analyte to the base material, while theunit having a hydrophobic group fulfills the role of binding thepolymeric compound to the base material.

The hydrophilic unit contained in the polymeric compound is typicallyrepresented by a phosphorylcholine group, and although there are noparticular limitations on the structure thereof, the unit represented bythe following general formula [1] most preferably has a structure inwhich a (meth)acrylic residue and a phosphorylcholine group are boundthrough a chain of alkylene oxide groups X having 1 to 10 carbon atomsas indicated by the left structural unit of the structural units. Inparticular, X is most preferably an ethylene oxide group. The number ofrepeating alkylene oxide groups in the formula is an integer of 1 to 20,and in the case the number of repeating units is 2 to 20, the number ofcarbon atoms of the repeating alkylene oxide groups may be the same ordifferent. Although 1 is inherently a natural number, it may berepresented as a component ratio of each constituent unit.

The component ratio of a unit having a phosphorylcholine group containedin the polymeric compound (ratio of 1 to the sum of l, m and n) ispreferably 5 mol % to 98 mol %, more preferably 10 mol % to 80 mol %,and most preferably 10% to 80% of all units of the polymeric compound.If the component ratio is below the lower limit value, hydrophilicitydiminishes and non-specific adsorption increases. On the other hand, ifthe component ratio exceeds the upper limit value, water solubilityincreases resulting in the possibility of the polymeric compound elutingduring an assay.

Although there are no particular limitations on the unit having ahydrophobic group contained in the polymeric compound of the presentinvention, the structure is preferably that in which a hydrophobic groupis bound to a (meth)acrylic group residue as is represented by themiddle structural unit of the structural units shown in theaforementioned general formula [1]. Although there are no particularlimitations thereon, examples of the hydrophobic group include alkylgroups and aromatics. The hydrophobic group is more preferably an alkylgroup in which the alkyl moiety has 2 to 10 carbon atoms. There are noparticular limitations on the structure of the alkyl group, and may belinear, branched or cyclic. As a result of a unit having a hydrophobicgroup being contained in the polymeric compound, wetting with respect toplastic and other hydrophobic base materials is improved, therebyenabling even coating. In addition, since hydrophobicity increases, thepolymeric compound can be prevented from eluting during an assay. In theformula, although m is inherently a natural number, it may berepresented as the component ratio of each constituent.

The component ratio of the unit having a hydrophobic group contained inthe polymeric compound (ratio of m to the sum of l, m and n) ispreferably 10 mol % to 90 mol %, more preferably 10 mol % to 80 mol %,and most preferably 20% to 80% of all units of the polymeric compound.If the component ratio exceeds the upper limit value, there is the riskof an increase in non-specific adsorption.

Although there are no particular limitations on the structure of theunit having a primary amino group contained in the polymeric compound ofthe present invention, the structure is preferably that connectedthrough a spacer Y containing a (meth)acrylic residue and an oxylaminoresidue. Z represents an oxygen atom in the case of an oxylamino group,while Z represents NH in the case of a hydrazide group. Although n isinherently a natural number, it may also be indicated as the componentratio of each component. Although there are no particular limitations onthe structure of the spacer Y containing an alkylene glycol residue, thestructure thereof is preferably represented by the following generalformula [2] or general formula [3], and is more preferably representedby general formula [2].

The component ratio of the unit having a primary amino group containedin the polymeric compound of the present invention (ratio of n to thesum of l, m and n) is preferably 1 mol % to 94 mol %, more preferably 2mol % to 90 mol %, and most preferably 20% to 40% of all units of thepolymeric compound. If the component ratio is below the lower limitvalue, the sugar chain can no longer be immobilized in an adequateamount. In addition, if the component ratio exceeds the upper limitvalue, non-specific adsorption increases.

Although there are no particular limitations on the method used tosynthesize the polymeric compound of the present invention, from theviewpoint of ease of synthesis, the production method preferably atleast comprises a step for radical copolymerizing a monomer having aphosphorylcholine group, a monomer having a hydrophobic group, and amonomer in which a primary amino group has been preliminarily protectedwith a protecting group, and a step for removing the protecting groupfrom the polymeric compound obtained in that step. Alternatively, theproduction method preferably at least comprises a step for radicalcopolymerizing a monomer having a phosphorylcholine group, a monomerhaving a hydrophobic group, and a monomer having a functional groupcapable of introducing a primary amino group, and a step for introducingthe primary amino group into the polymeric compound obtained in thatstep.

There are no particular limitations on the structure of the monomerhaving a phosphorylcholine group, and although examples include2-(meth)acryloyloxyethylphosphorylcholine,2-(meth)acryloyloxyethoxyethylphosphorylcholine,6-(meth)acryloyoxyhexylphosphorylcholine,10-(meth)acryloyloxyethoxynonylphosphorylcholine and2-(meth)acryloyloxypropylphosphorylcholine;2-methacryloyloxyethylphosphorylcholine is preferable from the viewpointof availability.

Specific examples of monomers having a hydrophobic group includen-butyl(meth)acrylate, iso-butyl(meth)acrylate, sec-butyl(meth)acrylate,t-butyl(meth)acrylate, n-neopentyl(meth)acrylate,iso-neopentyl(meth)acrylate, sec-neopentyl(meth)acrylate,neopentyl(meth)acrylate, cyclohexyl(meth)acrylate,n-hexyl(meth)acrylate, iso-hexyl(meth)acrylate, heptyl(meth)acrylate,n-octyl(meth)acrylate, iso-octyl(meth)acrylate,2-ethylhexyl(meth)acrylate, n-nonyl(meth)acrylate,iso-nonyl(meth)acrylate, n-decyl(meth)acrylate, iso-decyl(meth)acrylate,n-dodecyl(meth)acrylate, iso-dodecyl(meth)acrylate,n-tridecyl(meth)acrylate, iso-tridecyl(meth)acrylate,n-tetradecyl(meth)acrylate, iso-tetradecyl(meth)acrylate,n-pentadecyl(meth)acrylate, iso-pentadecyl(meth)acrylate,n-hexadecyl(meth)acrylate, iso-hexadecyl(meth)acrylate,n-octadecyl(meth)acrylate, iso-octadecyl(meth)acrylate andisononyl(meth)acrylate. Among these, cyclohexyl(meth)acrylate,n-butylmethacrylate, n-dodecylmethacrylate and n-octylmethacrylate aremost preferable.

Although there are no particular limitations on the structure of themonomer in which a primary amino group is preliminarily protected with aprotecting group, the structure is preferably that in which a(meth)acrylic group and an oxylamino group or a hydrazide group areconnected through a spacer Y containing an alkylene glycol residue asrepresented by the following general formula [4] (wherein, R3 representsa hydrogen atom or methyl group, Y represents a spacer containing analkylene glycol residue, Z represents an oxygen atom or NH, and Wrepresents a protecting group).

There are no restrictions on the protecting group W provided it is ableto protect an amino group, and any arbitrary protecting group can beused. In particular, a t-butoxycarbonyl group (Boc group),benzyloxycarbonyl group (Z group, Cbz group) or9-fluorenylmethoxycarbonyl group (Fmoc group) and the like are usedpreferably.

A specific example of this monomer is represented by the formulaindicated below.

Deprotection can be carried out under ordinary conditions iftrifluoroacetic acid, hydrochloric acid or anhydrous hydrofluoric acidis used.

On the other hand, although there are no restrictions on the method usedto introduce a primary amino group after having polymerized thepolymeric compound, the method is preferably a simple method that atleast consists of radical copolymerizing a monomer having aphosphorylcholine group, a monomer having a hydrophobic group, and amonomer having an alkoxy group, followed by reacting the alkoxy groupintroduced into the polymeric compound with hydrazine to form ahydrazide group. Preferable examples of the alkoxy group include amethoxy group, ethoxy group, propoxy group and t-butoxy group.

A specific example of this monomer is represented by the formulaindicated below.

The synthesis solvent of the polymeric compound of the present inventionmay be any solvent in which each monomer dissolves, and examples thereofinclude alcohols such as methanol, ethanol, isopropanol, n-butanol,t-butyl alcohol or n-pentanol; and benzene, toluene, tetrahydrofuran,dioxane, dichloromethane, chloroform, cyclohexanone,N,N-dimethylformamide, dimethylsulfoxide, methyl acetate, ethyl acetate,butyl acetate, methyl ethyl ketone, methyl butyl ketone, ethylene glycolmonoethyl ether, ethylene glycol monomethyl ether and ethylene glycolmonobutyl ether. One type of these solvents may be used alone or two ormore types may be used in combination.

An ordinary radical initiator may be used as polymerization initiator,and examples thereof include azo compounds such as2,2′-azobisisobutyronitrile (to be referred to as “AIBN”) or1,1′-azobis(cyclohexane-1-carbonitrile), and organic peroxides such asbenzoyl peroxide or lauryl peroxide.

The molecular weight of the polymeric compound of the present inventionis such that the number average molecular weight is preferably 5000 ormore and more preferably 10000 or more since this facilitates separationand purification of the polymeric compound and unreacted monomer.

Although deprotection can be carried out under ordinary conditions ifthe aforementioned trifluoroacetic acid, hydrochloric acid or anhydroushydrofluoric acid is used, the time at which deprotection is carried outis as indicated below.

Normally, deprotection is carried out at the stage the polymericcompound can be produced following completion of polymerization, and thepolymeric compound can be obtained by carrying out deprotectionfollowing completion of polymerization.

On the other hand, in the present invention, the property of inhibitingnon-specific adsorption of a sugar chain and the property ofimmobilizing a sugar chain can be easily imparted by coating thepolymeric compound onto the surface of a base material.

In this case, although a polymeric compound having a primary amino groupthat has been deprotected can also be coated, coating a polymericcompound having a highly reactive primary amino group after putting intosolution may cause the primary amino group to react during the procedureand be deactivated depending on the particular case.

Thus, it is preferable to purify the polymeric compound and coat ontothe surface of the base material immediately before deprotecting,followed by carrying out the deprotecting reaction to form a state inwhich the primary amino group is present on the surface of the basematerial.

Coating of the polymeric compound onto the surface of the base materialis carried out by, for example, preparing a polymeric solution obtainedby dissolving the polymeric compound in an organic solvent to aconcentration of 0.05% by weight to 50% by weight, coating onto thesurface of the base material using a known method such as immersion orspraying, and then drying either at room temperature or by heating.

Examples of organic solvents include alcohols such as methanol, ethanol,isopropanol, n-butanol, t-butyl alcohol, n-pentanol or cyclohexanol; andbenzene, toluene, tetrahydrofuran, dioxane, dichloromethane, chloroform,aceton, methyl acetate, ethyl acetate, butyl acetate, methyl ethylketone, methyl butyl ketone, ethylene glycol monoethyl ether, ethyleneglycol monomethyl ether, ethylene glycol monobutyl ether andcyclohexanone. One type of these solvents may be used alone or two ormore types may be used in combination. Among these, alcohols such asethanol, methanol, isopropanol, n-butanol, t-butyl alcohol, n-pentanolor cyclohexanol are preferable since they are dried easily withoutcausing degeneration of plastic base materials.

A slide plate, 96-well plate, container or microfluidic plate ispreferably used for the base material used in the present invention.Examples of these plates include a plastic plate, glass plate and platehaving metallic film. Specific examples of plastic plates include platesmade of materials such as polystyrene, cyclic polyolefin polymer,cycloolefin polymer, polypropylene, polyethylene, polysulfone,polyimide, polycarbonate or polymethyl methacrylate.

In particular, a plate made of cyclic polyolefin polymer or cycloolefinpolymer is useful as a base material used to observe fluorescence. Inthe case of using the aforementioned base materials, if the hydrophobicgroup of the polymeric compound is a cyclohexyl group, interaction withthe base material is favorable, and favorable results in terms of higheradsorbed amounts and lower background values are obtained in comparisonwith the case of coating a polymeric material of the same componentratio onto another base material (such as a polystyrene or glass basematerial).

In addition, in the case of coating the polymeric compound onto a cyclicpoluolefin polymer, coating is not possible for a polymeric compoundcontaining 100 mol % of an aminooxy monomer. On the other hand, althoughthe polymeric compound can be coated onto a polystyrene polymer, thislacks versatility since non-specific adsorption of impurities is notinhibited.

Examples of methods used to immobilize sugar chains on the base materialinclude a method consisting of spotting a solution in which a sugarchain or glycolipid (molecule in which a sugar chain is bound to alipid) has been dissolved onto the base material using a spotter, and amethod consisting of dispensing a solution in which a sugar chain orglycolipid has been dissolved into a container and the like andimmobilizing thereon.

It is necessary to form a reducing sugar moiety on the terminal portionof the sugar chain in the molecule in order to immobilize the sugarchain on the surface of the aforementioned base material. Although thereare no particular limitations on the oxidizing agent used, periodic acidcan be used. The concentration thereof is 0.04 M to 0.16 M. In addition,a sodium bicarbonate solution (pH 8.1) is normally used for the bufferof this oxidation reaction. The sugar chain can be chemicallyimmobilized by reacting an aldehyde group of a sugar chain oxidized inthis manner with a primary amino group on a plate to form a Schiff base.

In addition, in the case of immobilizing a sugar chain on a basematerial when in the form of a glycolipid, the glycolipid can also beimmobilized using the method described above by introducing a ketonegroup or aldehyde group into the lipid moiety instead of reducing thesugar chain and then using that group as a bonding point. Ozonolysis isan example of a method used to introduce a ketone group or aldehydegroup into the glycolipid moiety.

More specifically, ozone gas is introduced by bubbling for 30 minutesthrough 200 μL of a chloroform-methanol (1:1 (v/v)) solution of aglycolipid having a concentration of 200 μM. Subsequently, the gas isreplaced with nitrogen gas to remove the dissolved ozone. The ozonolysisreaction is stopped with 1 μL of triphenylphosphine (1 M toluenesolution). After evaporating the reaction solution, hexane is addedfollowed by stirring to obtain an ozonolysis product of the glycolipid(refer to reaction formula 1 indicated below).

Various types of buffers are preferably used for the solution in whichthe sugar chain or glycolipid is dissolved. Although there are noparticular limitations thereon, examples of buffers used include sodiumcarbonate, sodium hydrogen carbonate, potassium phosphate, dipotassiumhydrogen phosphate, Tris-hydrochloride buffer, Tris-acetate buffer, PBSbuffer, sodium citrate, sodium acetate, HEPES(N-2-hydroxyethylpiperazine-N′-ethanesulphonic acid) buffer and MOPS(3-(N-morpholino) propanesulfonic acid) buffer.

In the case of dissolving a sugar chain or glycolipid, the pH of thesolution is preferably 2 to 8. Although there are no particularlimitations on the concentration of the sugar chain or glycolipid in thesolution, it is preferably 0.0001 mg/ml to 10 mg/ml. The temperature atwhich the solution of sugar chain or glycolipid is immobilized ispreferably 0° C. to 100° C.

EXAMPLES

Although the following provides a more detailed explanation of thepresent invention based on an example and comparative example, thepresent invention is not limited to the following example.

Example

A cyclic polyolefin resin (hydrogenation product of a ring-openedpolymer of 5-methyl-2-norbornene, MFR (melt flow rate): 21 g/10 min,hydrogenation rate: substantially 100%, thermal deformation temperature:123° C.) was formed into the shape of a slide glass (dimensions: 75mm×25 mm×1 mm) to fabricate a solid substrate. This solid substrate wasimmersed in a 0.3% by weight ethanol solution of a copolymer consistingof 2-methacryloyloxyethylphosphorylcholine (MPC), n-butylmethacrylate(BMA) andN-[2-[2-[2-(t-butoxycarbonyl-aminooxyacetylamino)ethoxy]ethoxy]ethyl]-methacrylamide(OA) (ratio of each group as mol %: 26:66:8) followed by drying tointroduce a layer containing the aforementioned polymeric substance ontothe substrate surface.

Comparative Example

The solid substrate of the example was used without coating with thepolymeric substance.

(Immobilization of Glycolipid Sugar Chain)

Next, a solution prepared so that a sugar chain moiety of aganglioside-based glycolipid was present at a concentration of 0.5 mM in0.5 M acetate buffer was spotted onto the supports obtained in theexample and comparative example using an automated spotter followed byimmobilizing by allowing to stand undisturbed for 1 hour at 80° C. Thesupports were washed with ultrapure water following immobilization.

(Reaction with Sugar Chain-Binding Protein)

Next, a solution in which was dissolved a sugar chain-binding protein inthe form of labeled cholera toxin B subunit (Molecular Probes Inc.) wascontacted with the aforementioned washed supports at each of theconcentrations shown in Table 8 (solvent: Tris buffer containing 0.05%by weight Tween 20), followed by carrying out a sugar chain-proteinspecific reaction by allowing to stand undisturbed for 2 hours at roomtemperature. Following the reaction, each support was washed for 2minutes at room temperature using Tris buffer containing 0.05% by weightTriton X-100.

Fluorescence was measured for each of the spots on the supports as wellas portions other than the spots (background) of the example andcomparative example on which the aforementioned assay was carried out,followed by calculation of the difference between those values. Theresults are shown in Tables 7 and 8.

TABLE 7 At cholera toxin B subunit concentration of 2000 ng/mLGlycolipid Comparative Sugar Chain Example Example GM1a 746403 2038 GM21044 339 GM3 506 297 GD1a 37478 1116 GD2 899 274 GD3 444 198 GT1a 663621009 GT2 1021 458 GT3 345 96 (Values in table obtained by subtractingbackground value)

TABLE 8 Cholera toxin subunit B Comparative concentration ExampleExample 2000 ng/mL 746403 2010 200 ng/mL 422424 1527 20 ng/mL 78530 3042 ng/mL 32192 150 0.2 ng/mL 7647 22

A scanner manufactured by GE Healthcare Corp. (Typhoon TRIO+) was usedto measure fluorescence levels for the example and comparative example.Measurement conditions consisted of PMT voltage of 600 V, excitationwavelength of 532 nm, measuring wavelength of 580 nm, and resolution of25 μm.

In the case of the example, according to Table 7, only GM1a specificallybound with the cholera toxin B subunit, and according to Table 8,signals were able to be detected that were dependent on theconcentration of the cholera toxin B subunit. On the other hand, in thecase of the comparative example, there were no reactions at any of thesugar chain spots, and cholera toxin B subunit was unable to bedetected. Namely, the glycolipid sugar chain chip of the presentinvention can be said to have been able to detect protein bothspecifically and concentration-dependently.

INDUSTRIAL APPLICABILITY

Use of the sugar chain array of the present invention makes it possibleto efficiently detect an interaction between an analyte and a sugarchain. Since sugar chains are intimately involved in numerous vitalphenomena and the pathologies of cancer, infectious diseases and thelike, the sugar chain array of the present invention is able to greatlycontribute to, for example, the development of new diagnostic andtherapeutic methods.

1. A sugar chain array, comprising: a base material; and at least onesugar chain selected from the group consisting of sugar chains fromTables 1, 2, 3, 4, 5 and 6: TABLE 1 1 Glc Acyl1-O-6Glc 2 Galβ1-4Glc Xyl3 Gal Galα1-4Gal 4 GalNAcα1-3GalNAcβ1-3Galα1-4Gal Galα1-4Galβ1-4Glc 5Galα1-3Galα1-4Galβ1-4Glc Galα1-3Galα1-3Galα1-4Galβ1-4Glc 6Galα1-3Galα1-3Galα1-3Galα1-4Galβ1-4Glc GalNAcβ1-3Galα1-4Galβ1-4Glc 7GalNAcα1-3GalNAcβ1-3Galα1-3Galβ1-4Glc Galβ1-3GalNAcβ1-3Galα1-4Galβ1-4Glc8 GalNAcβ1-3Galα1-3Galα1-4Glc GalNAcβ1-3Galα1-3Galα1-3Galα1-4Glc 9GalNAcβ1-3Galα1-3Galα1-3Galα1-3Galα1- Galα1-3Galβ1-4Glc 4Galβ1-4Glc 10GalNAcβ1-3Galα1-3Galβ1-4Glc GlcNAcβ1-3Galβ1-4Glc 11Galβ1-3GlcNAcβ1-3Galβ1-4Glc Galβ1-4GlcNAcβ1-3Galβ1-4Glc 12Galα1-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc Galβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc 13Galα1-4Galβ1-4GlcNAcβ1-3Galβ1-4GlcGalβ1-4GlcNAcβ1-3Galβ1-4GlcNAcβ1-3Galβ1- 4Glc 14GalNAcβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc Galα1-3Galβ1-4GlcNAcβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc 15 Galβ1-4GlcNAcβ1-3(Galβ1-4GlcNAcβ1-GalNAcα1-3Galβ1-4GlcNAcβ1-3(Galβ1- 6)Galα1-4GlcNAcβ1-3Galβ1-4Glc4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4Glc 16Galα1-3Galβ1-4GlcNAcβ1-3(Galα1-3Galβ1-Galα1-3Galβ1-4GlcNAcβ1-3(Galα1-3Galβ1-4GlcNAcβ1-6)Galα1-4GlcNAcβ1-3Galβ1-4Glc4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3(Galα1- 3Galβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4Glc 17 GalNAcβ1-4Galβ1-4Glc Galβ1-3GalNAcβ1-4Galβ1-4Glc 18GlcNAcβ1-3(GalNAcβ1-4)Galβ1-4Glc Galα1-3Galβ1-4GlcNAcβ1-3(GalNAcβ1-4)Galβ1-4Glc 19 HSO3-3Glc HSO3-3Galβ1-4Glc 20 HSO3-3GalHSO3-3GalNAcβ1-3Galα1-4Galβ1-4Glc 21HSO3-3Galβ1-3GaNAcβ1-3Galα1-4Galβ1-4Glc GalNAcβ1-4(HSO3-3)Galβ1-4Glc 22HSO3-3GalNAcβ1-4(HSO3-3)Galβ1-4Gal Galβ1-3GalNAcβ1-4(HSO3-3)Galβ1-4Glc23 HSO3-3Galβ1-3GalNAcβ1-4Galβ1-4GlcHSO3-3Galβ1-3GalNAcβ1-4(HSO3-3)Galβ1- 4Glc 24 HSO3-6GlcNAcβ1-3Galβ1-4GlcGalβ1-4(HSO3-6)GlcNAcβ1-3Galβ1-4Glc 25HSO3-3GlcUAβ1-3Galβ1-4GlcNAcβ1-3Galβ1-HSO3-3GlcUAβ1-3(Galβ1-4GlcNAcβ1)₂- 4Glc 3Galβ1-4Glc 26HSO3-3Gal1-4Gal1-4Glc Fuc

TABLE 2 27 Fucα1-2Galβ1-4Glc GalNAcα1-3(Fucα1-2)Galβ1-4Glc 28Fucα1-2Galα1-3Galα1-4Galβ1-4Glc Fucα1-2Galβ1-3GalNAcβ1-3Galα1-4Galβ1-4Glc 29 Galβ1-4(Fucα1-3)GlcNAcβ1-6(Galβ1- Fucα1-2Galα1-3Galβ1-4Glc3)GalNAcβ1-3Galα1-4Galβ1-4Glc 30 Galα1-3(Fucα1-2)Galβ1-4GlcGalα1-3(Fucα1-2)Galβ1-3GalNAcβ1-3Galα1- 3Galβ1-4Glc 31Fucα1-2Galβ1-3GalNAcβ1-4Galβ1-4Glc Galα1-3Galβ1-3GalNAcβ1-4Galβ1-4Glic32 Galα1-3(Fucα1-2)Galβ1-3GalNAcβ1-3Galβ1-Fucα1-2Galβ1-3Glcp1-3Galβ1-4Glc 4Glc 33Galβ1-3(Fucα1-4)GlcNAcβ1-3Galβ1-4GlcGalα1-3(Fucα1-2)Galβ1-3GlcNAcβ1-3Galβ1- 4Glc 34GalNAcα1-3(Fucα1-2)Galβ1-3GlcNAcβ1-Fucα1-2Galβ1-3(Fucα1-4)GlcNAcβ1-3Galβ1- 3Galβ1-4Glc 4Glc 35Galα1-3(Fucα1-2)Galβ1-3(Fucα1- GalNAcα1-3(Fucα1-2)Galβ1-3(Fucα1-4)GlcNAcβ1-3Galβ1-4Glc 4)GlcNAcβ1-3Galβ1-4Glc 36Fucβ1-2Galβ1-4GlcNAcβ1-3Galβ1- Galβ1-3(Fucα1-4)GlcNAcβ1-3Galβ1-3GlcNAcβ1-3Galβ1-4Glc 3GlcNAcβ1-3Galβ1-4Glc 37Fucα1-2Galβ1-4(Fucβ1-3)GlcNAcβ1-3Galβ1-Fucα1-2Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1- 3GlcNAcβ1-3Galβ1-4Glc3(Fucα1-4)GlcNAcβ1-3Galβ1-4Glc 38 Fucα1-2Galβ1-3GlcNAcβ1-3(Fucα1-2Galβ1-GalNAcα1-3(Fucα1-2)Galβ1-3GlcNAcβ1-3(4)GlcNAcβ1-6)Galβ1-3GlcNAcβ1-3Galβ1-3(GalNAcα1-3(Fucα1-4)Galβ1-3GlcNAcβ1- 4Glc 6)Galβ1-3GlcNAcβ1-3Galβ1-4Glc39 GalNAcα1-3(Fucα1-2)Galβ1-3GlcNAcβ1-Fucα1-2Galβ1-4GlcNAcβ1-3Galβ1-4Glc 3(GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-6)Galβ1-3GlcNAcβ1-3Galβ1-4Glc 40 Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-4GlcGalα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-3Galβ1- 4Glc 41GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-Fucα1-2Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1- 3Galβ1-4Glc 4Glc 42Fucα1-2Galβ1-4GlcNAcβ1-3Galβ1- GalNAcα1-3(Fucα1-2)Galβ1-4(Fucα1-4GlcNAcβ1-3Galβ1-4Glc 3)GlcNAcβ1-3Galβ1-4Glc 43Galα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-3Galβ1-GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1- 4GlcNAcβ1-3Galβ1-4Glc3Galβ1-4GlcNAcβ1-3Galβ1-4Glc 44 Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-4(Fucα1-Fucα1-2Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1- 3)GlcNAcβ1-3Galβ1-4Glc4GlcNAcβ1-3Galβ1-4Glc 45 Fucα1-2Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-Fucα1-2Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1- 4GlcNAcβ1-3Galβ1-4Glc4(Fucα1-3)GlcNAcβ1-3Galβ1-4Glc 46 Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-Galβ1-4GlcNAcβ1-3Galβ1-4(Fucα1- 4GlcNAcβ1-3Galβ1-4Glc3)GlcNAcβ1-3Galβ1-4Glc 47 Galβ1-3GalNAcα1-3(Fucα1-2)Galβ1 -Galβ1-3(Fucα1-4)GlcNAcβ1-3Galβ1- 4GlcNAcβ1-3Galβ1-4Glc4GlcNAcβ1-3Galβ1-4Glc

TABLE 3 48 GalNAcα1-3(Fucα1-2)Galβ1-3GalNAcα1-Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1- 3(Fucα1-2)Galβ1-4GlcNAcβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc 4GlcNAcβ1-3Galβ1-4Glc 49Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-4(Fucα1-Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc3)GlcNAcβ1-3Galβ1-4(Fucα1-3)GlcNAcβ1- 3Galβ1-4Glc 50Galβ1-4GlcNAcβ1-3Galβ1-4(Fucα1- Fucα1-2Galβ1-4GlcNAcβ1-3(Fucα1-2Galβ1-3)GlcNAcβ1-(3Galβ1-4GlcNAcβ1)2-3Galβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4Glc 4Glc 51GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-Galα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-3(Galα1-3(GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1- 3(Fucα1-2)Galβ1-4GlcNAcβ1-6)Galβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4Glc 4GlcNAcβ1-3Galβ1-4Glc 52GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-Galα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-3Galβ1-3Galβ1-4GlcNAcβ1-3(GalNAcα1-3(Fucα1- 4GlcNAcβ1-3(Galα1-3(Fucα1-2)Galβ1-2)Galβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4Glc 3Galβ1-4Glc 53Galα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-3(Galα1- Fucα1-3GalNAcβ1-3Galα1-3Galβ1-3(Fucα1-2)Galβ1-4GlcNAcβ1-6)Galβ1- 4GlcNAcβ1-3(GlcNAcβ1-4)Galβ1-4Glc4GlcNAcβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc 54GalNAcα1-3(Fucα1-2)Galβ1-3Galβ1-4Galβ1-GalNAcα1-3(Fucα1-2)Galβ1-3(4)GlcNAcβ1- 4Glc 3Galβ1-4Glc 55GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-GalNAcα1-3(Fucα1-2)Galβ1-4Galβ1-3(Galβ1-3Galβ1-4GlcNAcβ1-3Galβ1-4Galβ1-4Glc 6)Galβ1-4Glc 56GalNAcα1-3(Fucα1-2)Galβ1-4Galβ1- GalNAcα1-3(Fucα1-2)Galβ1-3(GalNAcα1-3(GalNAcα1-3Galβ1-6)Galβ1-4Glc 3Galβ1-6)Galβ1-4Galβ1-4Glc 57GalNAcα1-3(Fucα1-2)Galβ1-4Galβ1- Galβ1-4(Fucα1-3)GlcNAcβ1-4Galβ1-3Galβ1-3(GlcNAcα1-4Galβ1-6)Galβ1-4Glc 4Glc 58GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1- GalNAcα1-3(Fucα1-2)Galβ1-4GlcNAcβ1-3(GlcNAcβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3(GlcNAcβ1-4GlcNAcβ1-4)(GalNAcα1- 4GlcNAcβ1-3(GlcNAcβ1-6)Galβ1-4Glc3(Fucα1-2)Galβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-4GlcNAcβ1-3(GlcNAcβ1-4Galβ1- 4GlcNAcβ1-3)Galβ1-4Glc 59GalNAcα1-3(Fucα1-2)Galβ1-3(4)GlcNAcβ1- NeuAcα2-3Gal3(Fucα1-2Galβ1-3(4)GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3(Galβ1-4GlcNAcβ1-3(Galβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-6)Galβ1- 4Galβ1-4Glc 60 NeuGcα2-3GalNeuAcα2-3Galβ1-4Glc 61 NeuGcα2-3Galβ1-4Glc NeuNH2α2-3Galβ1-4Glc 62Ac—O-4NeuGcα2-3Galβ1-4Glc NeuAcα2-8NeuAcα2-3Galβ1-4Glc 63NeuGcα2-8NeuAcα2-3Galβ1-4Glc NeuAcα2-8NeuGcα2-3Galβ1-4Glc 64NeuGcα2-8NeuGcα2-3Galβ1-4Glc Ac—O-9NeuAcα2-8NeuAcα2-3Galβ1-4Glc

TABLE 4 65 NeuAcα2-8NeuAcα2-8Neuα2-3Galβ1-4GlcAc—O-9NeuAcα2-8NeuAcα2-8NeuAcα2- 3Galβ1-4Glc 66GalNAcβ1-4(NeuAcα2-3)Galβ1-4Glc GalNAcβ1-4(NeuGcα2-3)Galβ1-4Glc 67Galβ1-3GalNAcβ1-4(NeuAcα2-3)Galβ1-4GlcGalβ1-3GalNAcβ1-4(NeuGcα2-3)Galβ1-4Glc 68Fucα1-2Galβ1-3GalNAcβ1-4(NeuAcα2- Fucα1-2Galβ1-3GalNAcβ1-4(NeuGcα2-3)Galβ1-4Glc 3)Galβ1-4Glc 69 Fucα1-3Galβ1-3GalNAcβ1-4(NeuAcα2-Galα1-3Galβ1-3GalNAcβ1-4(NeuAcα2- 3)Galβ1-4Glc 3)Galβ1-4Glc 70GalNAcβ1-4Galβ1-3GalNAcβ1-4(NeuAcα2-GalNAcα1-3GalNAcβ1-3Galβ1-3GalNAcβ1- 3)Galβ1-4Glc 4(NeuAcα2-3)Galβ1-4Glc71 Galβ1-3(Fucα1-2)Galβ1-3GalNAcβ1- Galβ1-3Galα1-3Galβ1-3GalNAcβ1-4(NeuAcα2-3)Galβ1-4Glc 4(NeuAcα2-3)Galβ1-4Glc 72Galα1-3Galβ1-3Galα1-3Galβ1-3GalNAcβ1-NeuAcα2-3Galβ1-3GalNAcβ1-4(NeuAcα2- 4(NeuAcα2-3)Galβ1-4Glc 3)Galβ1-4Glc73 NeuAc(NeuGc)α2-3Galβ1-3GalNAcβ1- NeuGcα2-3Galβ1-3GalNAcβ1-4NeuGcα2-4(NeuGc(NeuAc)α2-3)Galβ1-4Glc 3Galβ1-4Glc 74NeuAc9—O—Acα2-3Galβ1-3GalNAcβ1- GalNAcβ1-4(NeuAcα2-3)Galβ1-3GalNAcβ1-4(NeuAcα2-3)Galβ1-4Glc 4(NeuAcα2-3)Galβ1-4Glc 75NeuAcα2-8NeuAcα2-3Galβ1-3GalNAcβ1- GalNAcβ1-4(NeuAcα2-8NeuAcα2-3)Galβ1-4(NeuAcα2-3)Galβ1-4Glc 4Glc 76 Galβ1-3GalNAcβ1-4(NeuAcα2-8NeuAcα2-Fucα1-2Galβ1-3GalNAcβ1-4(NeuAcα2- 3)Galβ1-4Glc 8NeuAcα2-3)Galβ1-4Glc 77Galα1-3Galβ1-3GalNAcβ1-4(NeuAcα2- Galα1-3Galα1-3Galβ1-3GalNAcβ1-8NeuAcα2-3)Galβ1-4Glc 4(NeuAcα2-8NeuAcα2-3)Galβ1-4Glc 78Galα1-3(Fucα1-2)Galβ1-3GalNAcβ1- NeuAcα2-3Galβ1-3GalNAcβ1-4(NeuAcα2-4(NeuAcα2-8NeuAcα2-3)Galβ1-4Glc 8NeuAcα2-3)Galβ1-4Glc 79NeuAcα2-3Galβ1-3GalNAcβ1-4(NeuAc9—O— NeuAcα2-8NeuAcα2-3Galβ1-3GalNAcβ1-Acα2-8NeuAcα2-3)Galβ1-4Glc 4(NeuAcα2-8NeuAcα2-3)Galβ1-4Glc 80GalNAcβ1-4(NeuAcα2-8NeuAcα2-8NeuAcα2-Galβ1-3GalNAcβ1-4(NeuAcα2-8NeuAcα2- 3)Galβ1-4Glc 8NeuAcα2-3)Galβ1-4Glc81 NeuAcα2-3Galβ1-3GalNAcβ1-4(NeuAcα2-NeuAcα2-8NeuAcα2-3Galβ1-3GalNAcβ1- 8NeuAcα2-8NeuAcα2-3)Galβ1-4Glc4(NeuAcα2-8NeuAcα2-8NeuAcα2-3)Galβ1- 4Glc 82NeuAcα2-3Galβ1-3GalNAcβ1-4Galβ1-4GlcNeuGcα2-3Galβ1-3GalNAcβ1-4Galβ1-4Glc 83GalNAcβ1-4(NeuAcα2-3)Galβ1-3GalNAcβ1-GalNAcβ1-4(NeuGcα2-3)Galβ1-3GalNAcβ1- 4Galβ1-4Glc 4Galβ1-4Glc 84Galβ1-3GalNAcβ1-4(NeuGcα2-3)Galβ1-Galβ1-3(NeuAcα2-6)GalNAcβ1-4Galβ1-4Glc 3GalNAcβ1-4Galβ1-4Glc

TABLE 5 85 NeuAcα2-3Galβ1-3(NeuAcα2-6)GalNAcβ1-NeuAcα2-3Galβ1-3(NeuAcα2-8NeuAcα2- 4Galβ1-4Glc 6)GalNAcβ1-4Galβ1-4Glc 86NeuAcα2-8NeuAcα2-3Galβ1-3(NeuAcα2- NeuAcα2-8NeuAcα2-3Galβ1-3(NeuAcα2-6)GalNAcβ1-4Galβ1-4Glc 8NeuAcα2-6)GalNAcβ1-4Galβ1-4Glc 87NeuAcα2-3Galβ1-3(NeuAcα2-6)GalNAcβ1-NeuAcα2-3Galβ1-3GalNAcβ1-3Galα1-4Galβ1- 4(NeuAcα2-3)Galβ1-4Glc 4Glc 88NeuGcα2-3Galβ1-3GalNAcβ1-3Galα1-4Galβ1-NeuAcα2-8NeuAcα2-3Galβ1-3GalNAcβ1- 4Glc 3Galα1-4Galβ1-4Glc 89NeuGcα2-8NeuGcα2-3Galβ1-3GalNAcβ1- NeuAcα2-3Galβ1-3(NeuAcα2-6)GalNAcβ1-3Galα1-4Galβ1-4Glc 3Galα1-4Galβ1-4Glc 90NeuAcα2-3Galβ1-3GalNAcβ1-3Galα1-3Galβ1-NeuAcα2-3Galβ1-3GlcNAcβ1-3Galβ1-4Glc 4Glc 91NeuAcα2-3Galβ1-3(Fucα1-4)GlcNAcβ1- GalNAcβ1-4(NeuAcα2-3)Galβ1-3GlcNAcβ1-3Galβ1-4Glc 3Galβ1-4Glc 92 NeuAcα2-3Galβ1-3Galβ1-3GlcNAcβ1-3Galβ1-NeuAcα2-3Galβ1-3(NeuAcα2-6)GlcNAcβ1- 4Glc 3Galβ1-4Glc 93NeuAcα2-3Galβ1-3(Fucα1-4))(NeuAcα2- NeuAcα2-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc6)GlcNAcβ1-3Galβ1-4Glc 94 NeuGcα2-3Galβ1-4GlcNAcβ1-3Galβ1-4GlcNeuAcα2-6Galβ1-4GlcNAcβ1-3Galβ1-4Glc 95NeuAcα2-8NeuAcα2-3Galβ1-4GlcNAcβ1- NeuGcα2-8NeuGcα2-3Galβ1-4GlcNAcβ1-3Galβ1-4Glc 3Galβ1-4Glc 96 NeuAcα2-8NeuGcα2-3Galβ1-4GlcNAcβ1-NeuAcα2-8NeuAcα2-8NeuAcα2-3Galβ1- 3Galβ1-4Glc 4GlcNAcβ1-3Galβ1-4Glc 97GalNAcβ1-4(NeuAcα2-3)Galβ1-4GlcNAcβ1- NeuAcα2-3Galβ1-4(Fucα1-3)GlcNAcβ1-3Galβ1-4Glc 3Galβ1-4Glc 98 NeuAcα2-6Galβ1-4GlcNAcβ1-3(Galβ1-NeuAcα-3Galβ1-4GlcNAcβ1-3Galβ1- 4GlcNAcβ1-6)Galβ1-4Glc4GlcNAcβ1-3Galβ1-4Glc 99 NeuGcα2-3Galβ1-4GlcNAcβ1-3Galβ1-NeuAcα2-6Galβ1-4GlcNAcβ1-3Galβ1- 4GlcNAcβ1-3Galβ1-4Glc4GlcNAcβ1-3Galβ1-4Glc 100 NeuAcα2-3Galβ1-4GlcNAcβ1-(3Galβ1-NeuAcα2-3Galβ1-4GlcNAcβ1-3Galβ1- 4GlcNAcβ1)2-3Galβ1-4Glc4(Fucα1-3)GlcNAcβ1-3Galβ1-4Glc 101 NeuAcα2-3Galβ1-4GlcNAcβ1-3Galβ1-NeuAcα2-3Galβ1-4GlcNAcβ1-3Galβ1- 4(Fucα1-3)GlcNAcβ1-3Galβ1-4GlcNAcβ1-4(Fucα1-3)GlcNAcβ1-(3Galβ1-4GlcNAcβ1)2- 3Galβ1-4Glc 3Galβ1-4Glc 102NeuAcα2-3Galβ1-3GalNAcα1-3(Fucα1- NeuAcα2-3Galβ1-4GlNAcα1-3(Galβ1-2)Galβ1-4GlcNAcβ1-3Galβ1-4Glc 4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4Glc103 NeuAcα2-3Galβ1-4GlcNAcα1-3(Fucα1-NeuAcα2-3Galβ1-4GlcNAcα1-3(NeuAcα2- 2Galβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1- 3Galβ1-4Glc 3Galβ1-4Glc

TABLE 6 104 NeuAcα2-3Galβ1-4GlcNAcβ1-3Galβ1-NeuAcα2-3Galβ1-4GlcNAcβ1-3(NeuAcα2-3Galβ1-4GlcNAcβ1-3(6)(NeuAcα2-3Galβ1-4GlcNAcβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3(6)(NeuAcα2-3(6))Galβ1-4GlcNAcβ1-3Galβ1-4Glc3Galβ1-4GlcNAcβ1-3(6))Galβ1-4GlNAcβ1-3Galβ1- 4Glc 105NeuAcα2-3Galβ1-4GlcNAcβ1-3(Galα1-3Galβ1-NeuAcα2-3Galβ1-4GlcNAcβ1-3(GalNAcβ1-4GlcNAcβ1-6)Galβ1-4GlcNAcβ1-3Galβ1-4Glc 4)Galβ1-4Glc 106GalNAcβ1-4(NeuAcα2-3)Galβ1-4GlcNAcβ1- NeuAcα2-3Galβ1-3GalNAcβ1-4Glc3(GalNAcβ1-4)Galβ1-4Glc 107 GalNAcα1-3(Fucα1-2)Galβ1-3GalNAcβ1-Galα1-3(Fucα1-2)Galβ1-3GalNAcβ1-3Galα1- 3Galα1-4Galβ1-4Glc 4Galβ1-4Glc108 Neu5Acα2-3Galβ1-3GalNAcβ1-3Gal GalNAcα1-3GalNAcβ1-3Galα1-4Galβ1-4Glc

wherein, the sugar chain is immobilized on the base material.
 2. Thesugar chain array of claim 1, wherein the base material comprises acoating comprising a polymeric compound comprising a unit comprising aprimary amino group, and wherein a sugar chain is immobilized on thebase material by bonding the primary amino group to a reducing group onthe end of the sugar chain.
 3. The sugar chain array of claim 2, whereinthe polymeric compound further comprises a unit that maintainshydrophilicity and a unit comprising a hydrophobic group.
 4. The sugarchain array of claim 3, wherein the polymeric compound has formula [1]:

wherein: R1, R2, and R3 are each independently a hydrogen atom or methylgroup; R4 is a hydrophobic group; X is an alkyleneoxy group comprising 1to 10 carbon atoms; p is an integer from 1 to 20 and in the case that pis an integer of 2 to 20, the repeating X may be the same or different;Y is a spacer comprising an alkylene glycol residue; Z is an oxygen atomor NH; and l, m and n are each independently a natural number.
 5. Thesugar chain array of claim 4, wherein, in formula [1], Y has formula[2]:

wherein, q is an integer from 1 to 20; or Y has formula [3]:

wherein r is an integer from 1 to
 20. 6. The sugar chain array of claim2, wherein the primary amino group in the polymeric compound is anoxylamino group and/or hydrazide group.
 7. The sugar chain array ofclaim 6, wherein the content of the unit having a primary amino group inthe polymeric compound is from 20 mol % to 40 mol %, based on all unitsof the polymeric compound.
 8. The sugar chain array of claim 4, wherein,in formula [1], X is an ethyleneoxy group.
 9. The sugar chain array ofclaim 2, wherein the main chain of the polymeric compound is a(meth)acrylic backbone.
 10. The sugar chain array of claim 4, wherein,in formula [1], the hydrophobic group, R4, is an alkyl group comprising2 to 10 carbon atoms.
 11. The sugar chain array of claim 10, wherein, informula [1], the hydrophobic group, R4, is a cyclic alkyl group.
 12. Thesugar chain array of claim 11, wherein the cyclic alkyl group is acyclohexyl group.